US3631206A - Control of oxychlorination reactions - Google Patents

Control of oxychlorination reactions Download PDF

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US3631206A
US3631206A US554475A US3631206DA US3631206A US 3631206 A US3631206 A US 3631206A US 554475 A US554475 A US 554475A US 3631206D A US3631206D A US 3631206DA US 3631206 A US3631206 A US 3631206A
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oxychlorination
bed
reaction
temperature
cooling
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Lester E Bohl
Raymond M Vancamp
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PPG Industries Inc
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PPG Industries Inc
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
    • B01J8/1809—Controlling processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
    • B01J8/1836—Heating and cooling the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
    • B01J8/24—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles according to "fluidised-bed" technique
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
    • C07C17/158—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of halogenated hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00106—Controlling the temperature by indirect heat exchange
    • B01J2208/00115—Controlling the temperature by indirect heat exchange with heat exchange elements inside the bed of solid particles
    • B01J2208/00141—Coils
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B01J2208/00106—Controlling the temperature by indirect heat exchange
    • B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
    • B01J2208/00176—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles outside the reactor

Definitions

  • the present invention relates to the production of chlorinated hydrocarbons. More particularly, the present invention relates to the production of chlorinated hydrocarbons by processes involving the catalytic oxychlorination of hydrocarbons and/ or chlorohydrocarbons in fluidized beds.
  • oxychlorination refers to processes in which gaseous hydrogen chloride is utilized as a chlorinating agent.
  • the processes contemplated involve the reaction of gaseous hydrogen chloride, an oxygen containing gas such as air or elemental oxygen and the hydrocarbon and/or chlorohydrocarbon to be chlorinated while in contact with a metal halide catalyst. It has been postulated that the HCl in these reactions is oxidized to free chlorine and water and the chlorine reacts with the organic feed to produce a chlorinated hydrocarbon.
  • elemental chlorine is used as a feed gas in place of gaseous hydrogen chloride.
  • This latter process theoretically operates in a manner similar to the first except that an initial chlorination of the hydrocarbon and/or chlorohydrocarbon takes place.
  • free chlorine, an oxygen containing gas and the hydrocarbon or chlorohydrocarbon to be chlorinated are passed in contact with a metal halide catalyst.
  • the chlorine reacts with the hydrocarbon or chlorohydrocarbon to produce hydrogen chloride and a chlorinated derivative of the hydrocarbon and/ or chlorohydrocarbon.
  • Hydrogen chloride produced in this manner is then converted by oxidation to chlorine and water and its chlorine content again utilized to achieve additional chlorinations of the hydrocarbon and/or chlorohydrocarbon feed material.
  • the bed may assume a highly turbulent condition which in many ways resembles a boiling liquid.
  • These beds are termed in the art fluid beds.
  • the present process may be conducted with gas velocities that provide for dynamic and fluidized beds. The exact conditions requisite to establishing such bed conditions depends upon such factors as the particle size of the bed components, the gas velocity, density of the particles, etc.
  • Wilhelm & Kwauk. Chemical Engineering Process, volume 44, page 201 (1948) equate the various factors necessary for fluidizing a bed of solid particles and by following the principles therein discussed, the desired bed condition may be provided.
  • fluid beds are employed though it should be understood that in discussing fluid beds in the specification and claims applicants mean both highly turbulent beds and dynamic beds.
  • an effective method for removing heat from oxychlorination reactions conducted in fluid beds.
  • oxychlorination reactions may be conducted in fluidized bed reactors with a considerable reduction in the burning or oxidation normally encountered and a consequent increase in the yield of desired products.
  • considerable heat may be removed from reaction zones in which oxychlorination reactions are taking place by presenting to the reactant gases present in the oxychlorination reaction zones at least two cooling surfaces having different temperature conditions prevailing therein.
  • a relatively cold cooling surface is provided and operated at temperatures considerably below those necessary to maintain the oxychlorination reaction taking place within the bed.
  • a second surface is provided which operates at a temperature considerably higher than the first and removes a small quantity of heat from the reaction zone. This second surface at least in part operates at the threshold temperature necessary for the oxychlorination reaction being conducted.
  • the colder operating surface is controlled in its overall surface area so that the reaction taking place within the reaction zone is not quenched by the cooling action of this surface. Typically this cooler surface removes percent or more of the heat released inside the fluid bed.
  • a reactor 1 is provided and is surrounded by a jacket 2; located in the center of the reactor is a cooling coil 13.
  • the reactor is provided at the bottom portion with a gas introduction means or conduit 4 and the bottom of the reactor has a distributor plate 5 located therein for the distribution of gases fed to the wind box 6 through the reactor feed inlet 4.
  • the jacket 2 is maintained under pressure with a nitrogen purge placed upon a reflux condenser (not shown) and connected to the upper portion of the jacket through a line 8.
  • a suitable coolant medium such as boiling Dowtherm is circulated in the jacket, condensed in a reflux condenser and recirculated to the jacket through line 7.
  • a cyclone separator 9 Located in the upper portion of the reactor is a cyclone separator 9 provided with suitable gas inlets (not shown), and a dip leg 11, extending down into the fluidized bed.
  • the upper level of the fluidized bed is indicated by the numeral 12.
  • a cooling coil 13 is located in the central portion of the reactor and is connected to an inlet 14 and an outlet 15 for circulation of coolant into and out of the cooling coil.
  • reactor 1 is charged to a suitable level with the catalytic material usually a copper chloride-potassium chloride catalyst impregnated on a porous inert carrier as will be hereinafter more fully described.
  • the catalytic material usually a copper chloride-potassium chloride catalyst impregnated on a porous inert carrier as will be hereinafter more fully described.
  • the gaseous materials to be reacted that is, a hydrocarbon and/ or chlorohydrocarbon, an oxygen containing gas, and either HCl or elemental chlorine are introduced through line 4 via inlets 16, 17 and 18 into the wind box 6 and passed through the distributor plate 5 to the fluidized bed of particles contained in the reactor 1.
  • the velocity of the gases passing through the distributor plate dynamically suspends the particles contained in the bed and the bed height expands approximately to the level indicated by numeral 12 of the drawing.
  • the gases are fed to the reaction zone and upon contacting the catalyst reaction between the various components of the gas stream introduced takes place.
  • the exothermic heat of the reaction generated in the fluidized bed by contact of the gases with the catalytic material is removed by virtue of the operation of the jacket 2 and the cooling coils 13 located in the bed.
  • the cooling medium introduced through line 14 to the bed is preferably maintained at a temperature of 250 F. or less.
  • the coolant exiting from the cooling coil through line 15 is normally permitted to attain temperatures on the order of 240 F. to 280 F.
  • the jacket surrounding the reactor is maintained at temperatures conveniently on the order of 500 F. to 600 F.
  • the temperature differential between the cooling surface at the center of the bed and at the side of the reactor is usually 100 F. or more.
  • the exact temperature obtained in the cooling media will be varied depending upon the oxychlorination reaction being conducted in the fluidized bed.
  • the temperatures given above relate particularly to a fluidized bed reactor in which ethylene is being subjected to an oxychlorination reaction with HCl and air or oxygen for the production of 1,2-dichloroethane.
  • the temperature conditions in the cooling coil and reactor jacket will vary considerably.
  • the temperature differential between the jacket and the cooling coil located in the fluidized bed itself will always be maintained at least 100 F. preferably somewhere between 200 F. to 500 F.
  • the catalyst employed in conducting oxychlorination reactions in accordance with this invention are generally multivalent metal halides, particularly chlorides of metals such as copper, iron, chromium, etc. impregnated on a carrier.
  • metal halides particularly chlorides of metals such as copper, iron, chromium, etc. impregnated on a carrier.
  • copper containing oxychlorination catalysts are preferred, and a particularly eifective catalyst for conducting fluidized bed reactions in which oxychloriantion on procedures are encountered is a copper chloridepotassium chloride mixed catalytic material impregnated on a calcined fullers earth.
  • the selection of the particular carrier on which the metal salt or oxide is to be impregnated is somewhat variable and materials such as alumina, silica, 'kieselguhr, fullers earth, etc. may be employed.
  • a particularly effective carrier for conducting oxychlorination reactions involving fluid bed operations is Florex, (a calcined fullers earth manufactured by the Floridin Corporation).
  • Florex carrier impregnated with equal molar proportions of copper chloride and potassium chloride forms a preferred catalyst for conducting the fluid bed operations hereinafter described.
  • the fluid beds employed in accordance with the teachings of this invention typically contain catalyst particles ranging in size from 30-l00 mesh. Typically, the catalyst particles are maintained in the size range such that percent of the catalyst particles contained in the fluidized beds are between 240-600 microns in size.
  • the carrier particles are impregnated by immersion of the carrier in a solution containing the metal components.
  • a metal halide containing solution may be placed on the carrier particles while rotating the particles in a mixing or tumbling device.
  • a fluidized bed of carrier particles may be sprayed with a metal halide solution and enough heat supplied to the bed to evaporate the water of solution in order to accomplish desired deposition.
  • temperatures may be employed depending upon the ultimate hydrocarbon chloride product desired and the starting materials. These temperatures are well known to those skilled in the art. The precise temperature conditions employed will depend upon the hydrocarbon and/ or chlorohydrocarbon fed to the bed and the desired hydrocarbon chloride product. Generally speaking, fluidized beds in oxychlorination reactions are conducted at temperatures ranging from 470-1100 F.
  • aliphatic hydrocarbons containing from 1 to 4 carbon atoms and their incompletely chlorinated derivatives are fed in the gaseous phase along with oxygen and a chlorinating agent selected from the group consisting of HCl and C1 and mixtures of HCl and C1 to a catalytic oxychlorination reaction zone.
  • the velocity of the gases entering the zone are such that the entire bed of catalyst particles contained in the catalytic reaction zone is fluidized and the particles attain the state of random motion.
  • the reactions occurring in the fluidized bed are exothermic in nature and once the reaction has commenced, the circulating heat transfer medium located in the jacket surrounding the reaction zone and in the cooling coils immersed in the fluidized bed are so controlled that the desired reaction temperature for the reaction undergoing oxychlorination is readily achieved.
  • the heat transfer surfaces and the circulation of the cooling fluids are so designed that about 90 percent of the exothermic heat of reaction released in the bed is removed through the low temperature cooling surface contained in the bed itself.
  • the temperature of the other cooling surface surrounding the reaction zone is maintained at least in part at or near reaction temperatures so that operation of the cold surface does not in any way seriously impair the oxychlorination reaction or quench it.
  • the control of these heat transfer surfaces can be readily accomplished by recourse to automatic temperature control equipment in the form of temperature sensing devices located in thermowells inserted into the circulating cooling fluids and in the fluidized bed itself.
  • a nickel reactor 8 feet in height and 15 inches in diameter is employed as a fluid bed reactor.
  • the reactor is enclosed in a 20 inch diameter steel jacket forming an annular heat exchange system.
  • Dowtherm a diphenyldiphenyl oxide eutectic
  • An '8 inch nickel cyclone is located in the top of the reactor in a 20 inch diameter by 18 inch high expanded section.
  • Located in the bottom of the reactor is a nickel distributor plate having a plurality of drilled holes in it. Below the distributor plate is a chamber or box closed at the sides and bottom and serving as an introduction chamber for the reactant feed gases. Gas is introduced into the reactor by passing it through the chamber and the drilled holes of the distributor plate to the reactor proper.
  • the reactor is filled to a depth of 6 feet with catalyst particles which are prepared by dissolving 440 grams of copper chloride and 186 grams of potassium chloride in 1,000 cubic centimeters of water to form a stock solution.
  • catalyst particles which are prepared by dissolving 440 grams of copper chloride and 186 grams of potassium chloride in 1,000 cubic centimeters of water to form a stock solution.
  • Five hundred and eighty-six grams of stock solution prepared in this manner are diluted to 1533 cubic centimeters volume with distilled water and this diluted solution is utilized to supply catalyst to the carrier.
  • This solution is added to Florex (a calcined fullers earth) carrier particles 30 to 60 mesh (-U.S. sieve series) in size which are placed in a rototumbler.
  • the solution is added to the rototumbler in dropwise fashion and the rototumbler is continuously heated during the addition.
  • the impregnated Florex is dried in the rototumbler by rotating it for an additional 30 minutes and heating
  • the three gas feed lines provided for the introduction of oxygen, hydrocarbons and/or hydrocarbon chlorides, and a chlorinating agent are located in the bottom of the reactor.
  • a cooling coil consisting of 36 feet of /2 inch nickel pipe is located in the upper portion of the fluid bed and water under a pressure of 30 lbs. per square inch gauge is circulated through the coil to remove heat generated in the reaction zone.
  • the temperature of the water passed into the coil is varied between 200 F. to 220 F.
  • the reactor jacket is maintained at a temperature between 350 F. to 400 F.
  • ethylene, HCl and 6 oxygen are fed to the chamber of the reactor in a molar feed ratio of ethylene to HCl to oxygen of 1.0 to 2.0 to 0.58.
  • the superficial linear velocity of the gases fed to the reaction zone is 0.4 foot per second.
  • the bed temperature of the reactor is maintained at about 550 F. Operating the reactor in this manner ethylene is converted to ethylene dichloride in yields of 95 percent or better.
  • EXAMPLE II Utilizing the reactor of Example I and regulating the cooling coil in the center of the bed at temperatures between 220 F. to 240 F. and regulating the jacket temperature between 600 F. to 650 F., ethylene dichloride, HCl and oxygen are fed to the chamber of the reactor in a molar ratio of 1.0 to 1.1 to 1.2. The superficial linear velocity of the gases entering the reaction zone is 0.5 foot per second. The bed temperature in the zone is maintained between 750 F. to 850 F. Perchlorethylene and trichloroethylene are produced in this manner and utilizations of ethylene dichloride to chlorinated organics is percent while halide utilizations of percent are obtained.
  • EXAMPLE III Utilizing the equipment of Example I, 1,2-dichloroethane, chlorine and oxygen are fed to the reactor and reacted therein.
  • the jacket temperature is maintained at temperatures between 600 F. and 650 F.
  • the cooling coil temperature is regulated between 220 F. to 240 F.
  • the molar feed ratio of 1,2-dichloroethane to chlorine to oxygen is maintained at 1 to 0.6 to 1.05.
  • the superficial linear velocity of the gases entering the fluidized bed is regulated at 0.3 foot per second.
  • the bed temperature in the fluidized bed is maintained between 750 F. to 850 F. Operating under these conditions perchloroethylene and trichloroethylene are produced in good yields with the utilization of ethylene dichloride obtained of about 75 percent.
  • the colder surface located in the center of the fluidized bed where the gases are passed in rapid contact therewith, operates to remove the high heats of reaction released in very short periods of time thereby considerably reducing the hazards of high localized temperatures causing excess burning of hydrocarbon present in the bed at these points.
  • the utilization of a secondary cooling surface which operates at or near the threshold temperature of the reaction provides a means for heating particles which may be excessively cooled during passage through the center of the bed and at or near the cooling surface located therein to provide catalyst particles at the proper temperature for reaction with the various reactant gases fed thereto. In this manner the advantage of rapid cooling for the prevention of burning and the maintenance of optimum temperatures for reactions taking place within the fluidized bed is readily accomplished.
  • the cooling jacket or high temperature cooling surface will be maintained at temperatures typically 100 F. to 150 F. lower than the optimum reaction temperature for the specific hydrocarbon being oxychlorinated.
  • the low temperature cooling surface is at least 150 F. lower than the optimum reaction temperature, typically 200 F. to 400 F. lower.
  • a chlorination agent selected from the group consisting of HCl, C1 and mixtures of HCl and C1 are reacted in a fluidized bed of oxychlorination catalyst particles at an oxychlorination reaction temperature to produce a hydrocarbon chloride and to liberate heat, the improvement comprising: providing at least two cooling surfaces in contact with said fluidized bed, the first of said cooling surfaces being maintained at a temperature below that necessary to maintain the oxychlorination reaction taking place within the bed and at least 100 F.
  • the temperature of said second surface being low enough to remove heat from said fluidized bed but high enough to avoid a quenching of the reaction in said fluidized bed by said first surface, the temperatures of said surfaces being regulated by heat transfer from said surfaces to fluid heat transfer media which remain isolated from said fluidized bed.
  • the temperature of said second surface being low enough to remove heat from said fluidized bed but high enough to avoid a quenching of the reaction in said fluidized bed by said first surface, the temperatures of said surfaces being regulated by heat transfer from said surfaces to fluid heat transfer media which remain isolated from said fluidized bed.
  • the temperature of said second surface being low enough to remove heat from said fluidized bed but high enough to avoid a quenching of the reaction in said fluidized bed by said first surface, the temperatures of said surfaces being regulated by heat transfer from said surfaces to fluid heat transfer media which remain isolated from said fluidized bed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US554475A 1962-08-24 1966-06-01 Control of oxychlorination reactions Expired - Lifetime US3631206A (en)

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US (1) US3631206A (en(2012))
BE (1) BE635161A (en(2012))
CH (1) CH420090A (en(2012))
DE (1) DE1205080B (en(2012))
ES (1) ES288555A1 (en(2012))
FR (1) FR1357453A (en(2012))
GB (2) GB1027280A (en(2012))
NL (2) NL294389A (en(2012))
SE (1) SE304754B (en(2012))

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4329527A (en) * 1979-12-08 1982-05-11 Hoechst Aktiengesellschaft Process for the manufacture of 1,2-dichloroethane

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2641779B1 (fr) * 1988-12-26 1991-04-19 Atochem Procede et catalyseur d'oxychloration, leur application a la production du 1-2 dichloroethane
DE102009046301A1 (de) * 2009-11-02 2011-05-12 Highterm Research Gmbh Reaktor mit Kühleinrichtung

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1654821A (en) * 1923-11-14 1928-01-03 Holzverkohlungs Ind Aktien Ges Process for the chlorination of saturated hydrocarbons
FR937955A (fr) * 1948-12-07 1948-09-01 Nouveau procédé de chloruration catalytique et nouveau procédé de préparation de catalyseurs

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4329527A (en) * 1979-12-08 1982-05-11 Hoechst Aktiengesellschaft Process for the manufacture of 1,2-dichloroethane

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ES288555A1 (es) 1963-11-16
BE635161A (en(2012))
NL123729C (en(2012))
SE304754B (en(2012)) 1968-10-07
CH420090A (fr) 1966-09-15
DE1205080B (de) 1965-11-18
FR1357453A (fr) 1964-04-03
GB1027279A (en) 1966-04-27
GB1027280A (en) 1966-04-27
NL294389A (en(2012))

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